# Asylum, ICE in Charlotte & Michael Flynn $50 Million Claim

An episode of [Bloomberg Law](https://invisiblenetwork.ai/podcast/277975394), 17 Nov 2025, 39 min.

Audio: https://podtrac.com/pts/redirect.mp3/traffic.omny.fm/d/clips/e73c998e-6e60-432f-8610-ae210140c5b1/7c892d84-801f-4c0b-b0e9-ae2b0012ff5f/d7d9fb18-3703-4bf3-beef-b398018703ed/audio.mp3?utm_source=Podcast&in_playlist=91224201-26a6-429d-ac3c-ae2b0012ff6d

Immigration attorney Leon Fresco, a partner at Holland & Knight, discusses the immigration crackdown in Charlotte, NC, and the Supreme Court taking a case on the turning away of asylum seekers. Then Bloomberg legal reporter Zoe Tillman, discusses the Trump Justice Department starting up settlement talks with former Trump officials, Michael Flynn and Stefan Passantino. June Grasso hosts. See omnystudio.com/listener for privacy information.

## Transcript

[0:02] Speaker 1: This is Bloomberg Law with June Grossel from Bloomberg Radio.
[0:13] Speaker 2: Protests after masked ICE agents descended on Charlotte, North Carolina
[0:18] Speaker 2: over the weekend in the latest federal immigration crackdown in
[0:23] Speaker 2: a democratic city, Governor Josh Stein encouraged residents to stay
[0:28] Speaker 2: peaceful and to record any unusual interactions with ICE.
[0:33] Speaker 3: Everyone wants to be safe in their communities, but the
[0:37] Speaker 3: actions of too many federal agents are doing the exact opposite.
[0:41] Speaker 3: In Charlotte, We've seen masked, heavily armed agents and paramilitary
[0:45] Speaker 3: garb driving unmarked cars, targeting American citizens based on their
[0:50] Speaker 3: skin color, racially profiling and picking up random people in
[0:54] Speaker 3: parking lots and off of our sidewalks, going after landscapers,
[0:59] Speaker 3: simply decorating a Christmas tree in someone's front yard, and
[1:03] Speaker 3: entering churches and stores to grab people. This is not
[1:07] Speaker 3: making us safer. It's stoking fear and dividing our community.
[1:12] Speaker 2: My guest is immigration law expert Leon Fresco, a partner
[1:16] Speaker 2: at Hollanden Knight. Leon why the federal immigration cracked down
[1:21] Speaker 2: in Charlotte.
[1:22] Speaker 4: Well, basically, what's happened is that the administration has decided
[1:27] Speaker 4: that the pace of immigration enforcement is moving way too
[1:31] Speaker 4: slowly for its liking, and so it's going to try
[1:34] Speaker 4: to move its operations to cities where it can still
[1:37] Speaker 4: yield large numbers of people without status, but nevertheless does
[1:42] Speaker 4: not get the kind of friction that it has been
[1:45] Speaker 4: getting in cities where there is both United State government
[1:50] Speaker 4: and local government that is against the ICE immigration operations.
[1:55] Speaker 4: So what are the places that ICE has decided to
[1:59] Speaker 4: move operation to Is Charlotte, North Carolina, because again, even
[2:03] Speaker 4: though there is a lot of democratic local government they
[2:08] Speaker 4: are in the city, nevertheless it's still a more conservative
[2:11] Speaker 4: area of the country. The courts are in a more
[2:14] Speaker 4: conservative circuit, the fourth circuit, And so the idea is
[2:19] Speaker 4: that ICE would move its operation there to try to
[2:22] Speaker 4: again begin trying to establish precedent that it can use
[2:26] Speaker 4: reasonable suspicion to apprehend people and if necessary, plays people
[2:32] Speaker 4: into deportation proceedings. Meanwhile actually having large numbers of people
[2:37] Speaker 4: going in and doing fugitive operations as well. And so
[2:42] Speaker 4: you have that, but then you do have a democratic
[2:45] Speaker 4: governor there in North Carolina, and you have a democratic mayor,
[2:50] Speaker 4: and so from that standpoint, it's going to be very
[2:53] Speaker 4: interesting to see how this plays out of it'll play
[2:56] Speaker 4: out where they try to operate with the same script Chicago,
[3:01] Speaker 4: or will it play out because the courts in Charlotte
[3:03] Speaker 4: are not as progressive as the courts in Chicago were,
[3:09] Speaker 4: that this would be a great place to establish president
[3:12] Speaker 4: for the Trump administration that they can use their reasonable
[3:16] Speaker 4: suspicion and start apprehending people just who are generally walking
[3:21] Speaker 4: or at suspicious locations around Charlotte.
[3:26] Speaker 2: In a case that went to the Supreme Court on
[3:28] Speaker 2: the Emergency docket, the contention was that ICE was making
[3:34] Speaker 2: stops based on racial profiling, and the Supreme Court didn't
[3:39] Speaker 2: stop them from doing that, So what are they trying
[3:41] Speaker 2: to prove here?
[3:43] Speaker 4: Well, the difference is that in Chicago, there was an
[3:48] Speaker 4: order of operations that had been established by the District
[3:51] Speaker 4: Court that basically was still having ICE reporting to the
[3:55] Speaker 4: District Court with regard to having the use of body
[3:58] Speaker 4: cameras and and having transparency with regard to each of
[4:02] Speaker 4: its interactions with people and trying to figure out if
[4:07] Speaker 4: there really was reasonable suspicion for stops or was it
[4:11] Speaker 4: really all just racial profiling. And from that perspective, I
[4:17] Speaker 4: believe that even though the daily check ins with the
[4:20] Speaker 4: district judge were were not allowed any Further, I do
[4:23] Speaker 4: believe that perhaps there was this feeling that there had
[4:27] Speaker 4: been too much resistance in Chicago that it wasn't worth it.
[4:30] Speaker 5: To continue there.
[4:32] Speaker 4: And so I think the idea is try to go
[4:35] Speaker 4: to a jurisdiction that has similar yields of population in
[4:39] Speaker 4: order to be able to apprehend people, get the numbers
[4:41] Speaker 4: of deportation up, but that if that gets challenged, you
[4:45] Speaker 4: would be in the fourth Circuit, and the Fourth Circuit
[4:47] Speaker 4: is just demonstrably more conservative than the Seventh Circuit, and
[4:52] Speaker 4: then also the district judges in Chicago, and so the
[4:55] Speaker 4: idea would be that potentially good president for the t
[5:00] Speaker 4: administration could be established there with regard to how the
[5:04] Speaker 4: apprehensions are to be done, how people are to be
[5:06] Speaker 4: detained once they are apprehended, and the deportation of these
[5:11] Speaker 4: people once they are both apprehended and detained. And so
[5:16] Speaker 4: I believe that's what they're trying to accomplish here in Charlotte.
[5:19] Speaker 5: But we're gonna have.
[5:20] Speaker 4: To wait to see how this actually operates in practice.
[5:23] Speaker 2: The Border Protection Commander Gregory Bevino, who is the face
[5:27] Speaker 2: of Border patrol and has led the operations in La
[5:30] Speaker 2: Chicago and now Charlotte. Well, he admitted in a deposition
[5:35] Speaker 2: that he'd lied when he said he was hit by
[5:37] Speaker 2: a rock before he threw a canister of tear gas.
[5:41] Speaker 2: Did it seem like he sort of left Chicago because
[5:44] Speaker 2: a district judge was onto him.
[5:47] Speaker 4: Again, This is all part of they're going to try
[5:50] Speaker 4: to yield success in operations where they feel they can
[5:53] Speaker 4: yield success. And I do think it looks like the
[5:57] Speaker 4: operational crew that had started the operation in Chicago has
[6:01] Speaker 4: moved indeed to Charlotte for this operation that they're calling
[6:04] Speaker 4: Charlotte's Web, And they're trying to basically operate with these
[6:11] Speaker 4: reasonable suspicion based stops where they can say we're using
[6:15] Speaker 4: the criteria given by Supreme Court Justice Kavanov. You know
[6:20] Speaker 4: that as long as they are brief and they are contextual,
[6:23] Speaker 4: and they're not one hundred percent race based, but that
[6:27] Speaker 4: they have other factors in them, such as potentially known
[6:32] Speaker 4: presence in certain locations and known types of jobs that
[6:38] Speaker 4: people are congregating in where large yields of population of
[6:42] Speaker 4: people without status might be done, that those might be
[6:45] Speaker 4: considered reasonable suspicion, and so as long as they follow
[6:49] Speaker 4: that guidance, it appears that they'll be able to engage
[6:53] Speaker 4: in these operations. And then the question will be would
[6:56] Speaker 4: the Attorney General in North Carolina file any thing that
[7:01] Speaker 4: would actually challenge this? Would they end up getting similar
[7:03] Speaker 4: results from Chicago, where these operations ended up being very
[7:08] Speaker 4: closely scrutinized by the courts basically every single apprehension.
[7:13] Speaker 5: Or are they going to be allowed to.
[7:15] Speaker 4: Establish a president in Charlotte which they can then take
[7:17] Speaker 4: to other locations along the South, such as Memphis and
[7:22] Speaker 4: New Orleans and other places Atlanta where they might be
[7:26] Speaker 4: able to try to get different results than what had
[7:29] Speaker 4: been yielded in Chicago and Los Angeles.
[7:31] Speaker 2: Let me ask you this, are there any Republican cities
[7:35] Speaker 2: with large numbers of immigrants who are possibly there illegally?
[7:41] Speaker 2: Are there any Republican cities that the Trump administration can
[7:44] Speaker 2: go into or is it only democratic cities?
[7:47] Speaker 4: Well, I mean this is the issue is many of
[7:49] Speaker 4: the largest cities in America do not have Republican mayors.
[7:54] Speaker 5: So that's one of the problems.
[7:56] Speaker 4: They may have Republican governors, they may have Republican attorney general.
[8:00] Speaker 5: So you're thinking of, for.
[8:02] Speaker 4: Instance, in Texas, there's a lot of cities where you know,
[8:06] Speaker 4: you have democratic mayors, but you have the Republican governor
[8:09] Speaker 4: of Texas, you have the Republican attorney general. But in
[8:13] Speaker 4: terms of big cities, I mean maybe you have Dallas
[8:16] Speaker 4: might be one, or Fort Worth might be another. Oklahoma
[8:19] Speaker 4: City might be another, but it's not really a large
[8:23] Speaker 4: group of big cities that have Republican mayors. And so
[8:27] Speaker 4: I think there's some stat that says maybe eight out
[8:29] Speaker 4: of the largest fifty cities have Republican mayors, and the
[8:33] Speaker 4: three biggest ones are Fort Worth, Dallas in Oklahoma City.
[8:37] Speaker 4: So maybe they will go there, But the truth is
[8:39] Speaker 4: ICE is already operating pretty heavily in Texas, and so
[8:44] Speaker 4: there's not really much more that ICE can be doing
[8:46] Speaker 4: in Texas. With regard to Oklahoma City, I don't know.
[8:48] Speaker 4: Maybe they will try to go there, but that hasn't
[8:51] Speaker 4: been on the list of places there to go to
[8:54] Speaker 4: at the moment.
[8:55] Speaker 2: There was a story that you know, they're looking into
[8:58] Speaker 2: having an ICE facility on Staten Island. That's led to
[9:02] Speaker 2: speculation that after Zorimandami takes office as mayor of New
[9:08] Speaker 2: York that the administration is going to send ICE agents
[9:13] Speaker 2: into New York City the way it has in Chicago
[9:17] Speaker 2: and LA and Charlotte.
[9:20] Speaker 5: I'm not thinking this as part of any insight knowledge.
[9:22] Speaker 4: I'm just saying this is part of just knowledge generally
[9:24] Speaker 4: of how this system works. Is you would never try
[9:27] Speaker 4: to use the Coastguard facility on Staten Island to hold
[9:31] Speaker 4: detainees unless they one hundred percent happened to be from
[9:34] Speaker 4: New York City. And the reason for that is because
[9:38] Speaker 4: previously the detainees from New York used to get sent
[9:42] Speaker 4: to New Jersey. And the reason they would get sent
[9:45] Speaker 4: to New Jersey one it was obviously cheaper too logistically
[9:49] Speaker 4: there was.
[9:50] Speaker 5: More capacity at three.
[9:53] Speaker 4: The Second Circuit is considered normally more liberal than the
[9:58] Speaker 4: Third Circuit, even though Third tart that had been liberal
[10:01] Speaker 4: in some instances. Normally, the Third Circuit is considered a
[10:05] Speaker 4: more conservative court than the Second Circuit, so that once
[10:08] Speaker 4: you detain people in New York City and you move
[10:11] Speaker 4: them over to the Third Circuit, you're much more likely
[10:14] Speaker 4: to get a conservative opinion in whether it's a detention case,
[10:17] Speaker 4: a removal case, or anything else. Putting them in Staten
[10:21] Speaker 4: Island then subjects you not just to the Second Circuit,
[10:26] Speaker 4: but also to the Southern District of New York. And
[10:29] Speaker 4: the Southern District of New York is a very, very
[10:32] Speaker 4: progressive court. It's not at all like almost any other
[10:36] Speaker 4: court in America because you've had two Democratic senators in
[10:39] Speaker 4: New York for decades and they have had great influence
[10:43] Speaker 4: over the judges that have been appointed in New York.
[10:46] Speaker 4: And so it's very, very unlikely that any good case
[10:52] Speaker 4: law would come out of detaining people in Staten Island.
[10:55] Speaker 4: And so the only reason you would do it is
[10:58] Speaker 4: to say, we are going to have a major crackdown
[11:01] Speaker 4: in New York City, and this is space that we
[11:04] Speaker 4: want in order to engage in that correctown.
[11:07] Speaker 2: Well, I hope you're right about that. Leon. Coming up
[11:09] Speaker 2: next on the Bloomberg Lanne Show, the Supreme Court agreed
[11:13] Speaker 2: today to review an immigrant's right to seek asylum at
[11:17] Speaker 2: the border. I'm June Grosso and you're listening to Boomberg.
[11:21] Speaker 2: The Supreme Court has agreed to review the policy of
[11:25] Speaker 2: denying migrants the chance to apply for asylum if they
[11:29] Speaker 2: haven't set foot on American soil, in the practice known
[11:33] Speaker 2: as metering border agents turn back potential asylum seekers before
[11:39] Speaker 2: they cross into the US to limit the numbers seeking asylum.
[11:43] Speaker 2: The Ninth Circuit ruled that The Ninth Circuit ruled that
[11:47] Speaker 2: metering violates the migrants' constitutional rights and a federal law
[11:52] Speaker 2: requiring officials to screen anyone who shows up at ports
[11:56] Speaker 2: of entry seeking asylum. The Trump administration and appeal that
[12:01] Speaker 2: decision to the Supreme Court. I've been talking to immigration
[12:04] Speaker 2: attorney Leon Fresco of Holland and Knight.
[12:08] Speaker 4: Leon.
[12:08] Speaker 2: There are a couple of legal fights going on over asylum.
[12:13] Speaker 4: There's a lot of different parts of the asylum system
[12:16] Speaker 4: that are all eventually going to work their way up
[12:19] Speaker 4: to the Supreme Court. The most important one not being
[12:22] Speaker 4: this case, but just being generally the case that will
[12:26] Speaker 4: discuss whether by executive fiat, the president has the authority
[12:31] Speaker 4: to basically end asylum in the United States for people
[12:35] Speaker 4: who cross the border illegally. That case is working its
[12:41] Speaker 4: way up, and there's DC case law talking about that
[12:46] Speaker 4: the Trump administration may not have the authority to unilaterally
[12:50] Speaker 4: do that To just say if you cross the border illegally,
[12:53] Speaker 4: you can't get asylum.
[12:54] Speaker 5: This is slightly different.
[12:55] Speaker 4: This then would say, because when you have that discuss
[13:00] Speaker 4: that we just talked about, can you get asylum if
[13:02] Speaker 4: you cross the border illegally. There's a talking point that
[13:05] Speaker 4: then gets offered by the people who don't want individuals
[13:10] Speaker 4: crossing the border illegally to get asylum. They say, why
[13:15] Speaker 4: don't you do it the right way and go to
[13:17] Speaker 4: a port of jury. So everybody says, well, gee, that
[13:21] Speaker 4: certainly makes a lot of sense. Do it the right way,
[13:23] Speaker 4: go to a port of entry. Don't just run across
[13:25] Speaker 4: the border and cause chaos, you know, present yourself to
[13:28] Speaker 4: someone who's there, who's prepared, ready to examine the case,
[13:32] Speaker 4: et cetera.
[13:33] Speaker 5: So far, so good.
[13:34] Speaker 4: But there have been policies in both the Trump administration
[13:38] Speaker 4: and the Biden administration that say, hold on, we're not
[13:41] Speaker 4: going to let you go in through the port of
[13:43] Speaker 4: entry either because whether it was COVID or just they
[13:46] Speaker 4: don't want people going through the port of entry. We
[13:49] Speaker 4: don't want that either. We don't want anybody coming in
[13:51] Speaker 4: from the southern border asking for asylum. So here then
[13:55] Speaker 4: comes the question if that human being had come across
[14:01] Speaker 4: the port of entry and entered in the US side
[14:04] Speaker 4: of the port of entry, we'd be in the same
[14:07] Speaker 4: situation we were in when we're talking about the person
[14:09] Speaker 4: who illegally crosses. Then we're just in that Supreme Court
[14:14] Speaker 4: land that we don't know where it's gonna end up,
[14:16] Speaker 4: which can be executive by FIAT ban people from coming
[14:20] Speaker 4: in for asylum. Okay, there's that one, but this is different.
[14:25] Speaker 4: This is what if the US gets to you physically
[14:28] Speaker 4: while you're on the Mexican side of the port of entry,
[14:31] Speaker 4: so your body never makes it to the US. Are
[14:34] Speaker 4: you still eligible to apply for asylum or has the
[14:38] Speaker 4: US basically made it impossible for you to go into court?
[14:42] Speaker 4: Because it would be the same thing as if you
[14:45] Speaker 4: were saying, why can't I apply for asylum from New
[14:48] Speaker 4: Zealand or from Australia.
[14:50] Speaker 5: I don't get it.
[14:50] Speaker 4: I should just be allowed to just announce that I
[14:53] Speaker 4: have an asylum claim to some American at an embassy
[14:56] Speaker 4: and in Australia or in New Zealand. Should be allowed
[15:00] Speaker 4: to do that. And if I'm not allowed to do that,
[15:02] Speaker 4: I should be able to sue in court that's not allowed.
[15:05] Speaker 4: You can't if you live in New Zealand just go
[15:07] Speaker 4: to a US embassy and ask for an asylum or
[15:10] Speaker 4: you can't if you live in Australia, go to a
[15:12] Speaker 4: US embassy and ask for asylum, and if they say no,
[15:15] Speaker 4: go to a federal court. But the Ninth Circuit said
[15:18] Speaker 4: that if you get stopped on the Mexican side of
[15:21] Speaker 4: the US port of entry, if you're trying to arrive
[15:25] Speaker 4: in the United States and the only reason you don't
[15:28] Speaker 4: arrive is because the US stops you from arriving, that
[15:33] Speaker 4: that would still be considered an arrival in the United
[15:37] Speaker 4: States for the purpose of triggering all of these asylum
[15:40] Speaker 4: questions about whether you're eligible to apply for asylum, whether
[15:44] Speaker 4: the US can't let you stay in Mexico, they have
[15:47] Speaker 4: to bring you in if you have a credible fear,
[15:49] Speaker 4: they have to let you make your case in the
[15:51] Speaker 4: United States.
[15:53] Speaker 5: And so that's really the issue. Now.
[15:56] Speaker 2: They're not using this metering process. So why is the
[15:59] Speaker 2: Trump ad minntest bothering to appeal it to the Supreme Court?
[16:03] Speaker 4: The Trump administration decided because I think what happens is
[16:08] Speaker 4: they're concerned that the current administrative ban that they have
[16:13] Speaker 4: on asylum might be taken away, and if that happens,
[16:19] Speaker 4: then they're going to try to say, well, you know,
[16:21] Speaker 4: go in through the port of entry, but again limiting
[16:26] Speaker 4: who can come in through the port of entry. So
[16:28] Speaker 4: they're going to want the discretion to be able to say, look,
[16:31] Speaker 4: we're letting in some people through the port of entry
[16:34] Speaker 4: to apply for asylum each day, but if you're not
[16:37] Speaker 4: one of the fifty people, let's say, because they're going
[16:40] Speaker 4: to try to make the number low, if you're not
[16:42] Speaker 4: one of the fifty people that's letting him in, just
[16:44] Speaker 4: because we apprehend you on the Mexican side of the
[16:47] Speaker 4: border doesn't mean you've now succeeded in being able to
[16:50] Speaker 4: make an asylum claim.
[16:52] Speaker 5: And so the.
[16:54] Speaker 4: Ninth Circuit had said, yes, that person should be given
[16:56] Speaker 4: the right.
[16:57] Speaker 5: To apply for asylum.
[16:59] Speaker 4: But what subsequently happened is the Biden administration took away
[17:03] Speaker 4: that policy, and so the immigrants' rights advocates are saying,
[17:07] Speaker 4: this is mood, this is not a thing anymore, because
[17:09] Speaker 4: the Trump administration really isn't relying on this.
[17:12] Speaker 5: They're relying on the.
[17:13] Speaker 4: Nobody gets asylum in the Southern Border period executive fiat.
[17:18] Speaker 4: They're not relying on this argument anymore about we've apprehended
[17:21] Speaker 4: you at the port of entry, so it's mood, you
[17:24] Speaker 4: shouldn't decide this. But the Trump administration is trying to
[17:27] Speaker 4: say it's not moot, and it looks like the Supreme
[17:30] Speaker 4: Court has agreed that it's not mood that they want
[17:33] Speaker 4: to actually come to a decision, which I believe if
[17:36] Speaker 4: they've taken cert means they're very likely to overturn the
[17:40] Speaker 4: Ninth Circuit's decision that says that if you are in
[17:44] Speaker 4: Mexico and trying to arrive in the US, you have
[17:47] Speaker 4: basically succeeded in presenting yourself for an asylum claim. I
[17:51] Speaker 4: think they will overturn that, it seems like, and they
[17:54] Speaker 4: will say no, no, no, your body actually has to
[17:56] Speaker 4: make it into the US in order to trigger your
[18:00] Speaker 4: rights to apply for asylum. Otherwise, where do we draw
[18:04] Speaker 4: the line again? Can you do this in Australia, Can
[18:07] Speaker 4: you do this in New Zealand, etc.
[18:08] Speaker 5: Etc.
[18:09] Speaker 2: I don't think there are too many people in Australia
[18:12] Speaker 2: or New Zealand right now trying to get asylum in
[18:16] Speaker 2: the United States.
[18:18] Speaker 5: Or the Ocean period.
[18:19] Speaker 4: You know, if you're coming in and you're two miles
[18:21] Speaker 4: out from the US and we interdict you, does that
[18:24] Speaker 4: mean you've succeeded and now you can apply for asylum.
[18:26] Speaker 4: And so those are the tough questions here.
[18:29] Speaker 2: So let's turn to this on Bank ruling from the
[18:33] Speaker 2: DC Circuit Court of Appeals. It's a little confusing. So
[18:36] Speaker 2: this goes back to the situation where Judge Boseburg was
[18:41] Speaker 2: trying to figure out whether or not the Trump administration
[18:45] Speaker 2: was sending Venezuelans to El Salvador, to that prison in
[18:49] Speaker 2: l Salvador, and he asked them to turn around whatever
[18:53] Speaker 2: flights are on their way, and the question is whether
[18:57] Speaker 2: they lied to him correct.
[19:00] Speaker 4: This is sort of two separate cases. The first case
[19:04] Speaker 4: is about the substance of whether a habeas petition could
[19:08] Speaker 4: be used to challenge the fact that a law from
[19:12] Speaker 4: seventeen ninety eight called the Alien Enemies Act allowed the
[19:15] Speaker 4: government to basically identify anyone had thought was a foreign
[19:18] Speaker 4: national and send them to El Salvador so long as
[19:22] Speaker 4: they thought that person was an enumerated gang member from
[19:26] Speaker 4: trend to Ragua, Venezuela because they said that that was
[19:29] Speaker 4: an alien enemy. So there was a lot of things
[19:31] Speaker 4: to review. Conceivably, are you an American or not? Are
[19:35] Speaker 4: you trend to Aragua or not? Does this allow you
[19:38] Speaker 4: to get sent to El Salvador all of these things,
[19:40] Speaker 4: and that's still working its way through the courts about
[19:43] Speaker 4: the constitutionality of all of this. But what the Supreme
[19:46] Speaker 4: Court ultimately said is a habeas in DC is the
[19:50] Speaker 4: wrong place to do this, or an administrative procedure at
[19:53] Speaker 4: case in DC is also the wrong place to do this.
[19:56] Speaker 4: You've got to do it in the district in which
[19:59] Speaker 4: the person was detained. And so they sent those cases
[20:03] Speaker 4: to Texas and other places where the people who were
[20:06] Speaker 4: going to be sent to Venezuela were actually detained. And
[20:10] Speaker 4: you know, there's a lot of debate about how much
[20:11] Speaker 4: time you have to file one.
[20:13] Speaker 5: Of these cases, et cetera.
[20:14] Speaker 4: So that's case number one, the substance, but case number two,
[20:18] Speaker 4: the sort of what I would call the anciliary part
[20:22] Speaker 4: of the case, would be that the judge was upset
[20:27] Speaker 4: with how the substance was argued, even though the judge
[20:30] Speaker 4: apparently doesn't have jurisdiction to view any of the substance anymore.
[20:34] Speaker 4: Of this case, the judge said, when I thought I did,
[20:37] Speaker 4: and when everybody thought I did, you the government engage
[20:42] Speaker 4: in actions that I'm worried violated content of court. And
[20:46] Speaker 4: so then there was an appeal about, well, can the
[20:49] Speaker 4: court continue along these lines of trying to hold the
[20:53] Speaker 4: government in criminal content and to identify the officials who
[20:58] Speaker 4: the court is concerned may or may not have made
[21:01] Speaker 4: misrepresentations to the court about flights to El Salvador that
[21:05] Speaker 4: were or weren't happening, or should or shouldn't have been happening.
[21:09] Speaker 4: And then they were potentially stonewalling the court about not
[21:12] Speaker 4: wanting to give information about who did what, who said what,
[21:16] Speaker 4: et cetera.
[21:18] Speaker 5: And so what happened.
[21:20] Speaker 4: Was was there was a appeal where the government said, look,
[21:24] Speaker 4: we're done with the District Court Judge just Boseburg here
[21:28] Speaker 4: and we're trying to get what's called the rid of
[21:30] Speaker 4: man damis saying we don't want to be part of
[21:33] Speaker 4: this anymore. We don't want to have to talk to
[21:35] Speaker 4: Judge Bosburg about identifying responsible officials, naming them, saying what
[21:41] Speaker 4: they did, et cetera. What happened was there was a
[21:44] Speaker 4: two to one decision from the Court of Appeals in
[21:47] Speaker 4: BC saying that okay, fine, Judge Boseburg, We're gonna grant
[21:53] Speaker 4: what's called a writ of mandamus, which is very very
[21:56] Speaker 4: rare where the court basically stops another judge from doing something,
[22:01] Speaker 4: And what the DC Circuit said two to one is
[22:04] Speaker 4: we're going to just stop the judge from trying to
[22:06] Speaker 4: identify responsible officials in order to maybe hold them in
[22:10] Speaker 4: criminal content. So then the plaintiffs in the case, who
[22:14] Speaker 4: are the people representing the El Salvador and deportees who
[22:19] Speaker 4: are Venezuelan, they petitioned for rehearing and bank saying that's
[22:24] Speaker 4: not fair that the court should be able.
[22:25] Speaker 5: To hold the government in content.
[22:28] Speaker 4: And so the issue again in this case was well,
[22:31] Speaker 4: was the panel correct to issue this rid ofm man
[22:33] Speaker 4: damus against the judge, And the en banc panel did
[22:37] Speaker 4: say yes, the panel was correct in issuing mandamus against
[22:42] Speaker 4: the judge. But there were several judges in the DC
[22:47] Speaker 4: Circuit who expressed serious concerns about what they felt was
[22:50] Speaker 4: government misconduct, and so they said, look, let Judge Bozburg
[22:57] Speaker 4: continue on with his content in and yes, he can't
[23:02] Speaker 4: go and start trying to go through every single part
[23:06] Speaker 4: of who knows what and.
[23:07] Speaker 5: Who did what. But at the end of the day,
[23:10] Speaker 5: if specific lawyers that.
[23:11] Speaker 4: Were in front of him did lie to him, he
[23:14] Speaker 4: can and should be able to move forward with a
[23:17] Speaker 4: contemp proceeding, and so we're gonna have to wait and
[23:20] Speaker 4: see if that actually ends up being the case or not.
[23:23] Speaker 4: But he's gonna have a hearing and they're gonna go
[23:25] Speaker 4: back and look at that specific issue. So maybe not
[23:28] Speaker 4: go through and start sanctioning all of the government officials
[23:32] Speaker 4: that may have been involved in the deportation itself, but
[23:36] Speaker 4: at least the lawyers who went in, if there were
[23:39] Speaker 4: any that actually made this representation to Judge Bozburg, those
[23:43] Speaker 4: might actually still end up being in contempt unless a
[23:46] Speaker 4: future order comes from either the DC Circuit or the
[23:51] Speaker 4: Supreme Court that says no, no, no, We're.
[23:54] Speaker 5: Done with all of this.
[23:56] Speaker 4: But they did an issue We're done with all of
[23:58] Speaker 4: this order, so the issue still continues, oddly enough, in
[24:03] Speaker 4: this bizarre context.
[24:05] Speaker 2: It is a long and winding case. Thanks as always, Leon.
[24:09] Speaker 2: That's Leon Fresco of Holland and Knight. Coming up next,
[24:13] Speaker 2: the Justice Department's sudden settlement talks with former Trump officials.
[24:17] Speaker 2: This is Bloomberg. The Justice Department has been discussing settlements
[24:24] Speaker 2: with two former officials from Donald Trump's first term, who,
[24:28] Speaker 2: like the President, claim their owed multimillion dollar payouts from
[24:32] Speaker 2: the US government as victims of politically motivated actions. Trump's
[24:38] Speaker 2: first national security advisor, Michael Flynn and former senior White
[24:42] Speaker 2: House lawyer Stefan Pasantino have been in talks with the
[24:46] Speaker 2: Trump administration since at least late summer. The negotiations mark
[24:51] Speaker 2: a shift from the Justice Department's position during the Biden administration,
[24:56] Speaker 2: where government lawyers successfully fought both cases. Joining me is
[25:01] Speaker 2: Bloomberg News reporter Zoe Tillman, Who's been looking into these negotiations. So, Zoe,
[25:07] Speaker 2: why are Flynn and Pasentinos suing the government?
[25:11] Speaker 1: So they have two very different lawsuits stemming from two
[25:15] Speaker 1: sort of very different big investigations surrounding Trump and Trump World.
[25:21] Speaker 1: Michael Flynn is the older case. He was Trump's first
[25:25] Speaker 1: national security advisor for a very brief moment in time,
[25:29] Speaker 1: and then faced prosecution by the Special Counsel Robert Muller
[25:34] Speaker 1: in connection with the Russia probe, where he was charged
[25:37] Speaker 1: with lying to investigators pretty early on in that investigation,
[25:42] Speaker 1: sort of pre Muller's appointment about his contacts during the
[25:47] Speaker 1: twenty sixteen twenty seventeen transition period with a Russian official,
[25:51] Speaker 1: and at first Michael Flynn pleaded guilty, entered a plea deal,
[25:56] Speaker 1: admitted lying, but then changed course dramatically hard one eighty.
[26:01] Speaker 1: He brought on new lawyers, Sidney Powell, who would go
[26:04] Speaker 1: on to become sort of a very bold face name,
[26:07] Speaker 1: but was not really in the spotlight at the time,
[26:10] Speaker 1: and you know, backtracked on that and fought the prosecution
[26:14] Speaker 1: tooth and nail and wound up having his case dismissed
[26:18] Speaker 1: by then A G. Bill Barr. He was subsequently full
[26:23] Speaker 1: out pardoned by Trump near the end of his first term.
[26:26] Speaker 1: So Michael Flynn sued and said this was a malicious prosecution,
[26:30] Speaker 1: this was an unlawful targeting of me, and he was
[26:35] Speaker 1: seeking fifty million dollars for the harms that he suffered
[26:38] Speaker 1: for that. So Trump loses the election. January sixth happened.
[26:43] Speaker 1: There's then a congressional investigation into January sixth, and Stefan
[26:47] Speaker 1: Pasentino is a lawyer for a number of witnesses who
[26:51] Speaker 1: are called as part of that investigation. At least some
[26:54] Speaker 1: of them are being paid by a Trump affiliated pack
[26:57] Speaker 1: and his clients include Cassidy Hutchinson, who was a former
[27:01] Speaker 1: White House aide to Mark Meadows, and he represented her,
[27:06] Speaker 1: and then he didn't represent her. She gets new lawyers
[27:09] Speaker 1: and goes on to testify in front of a nationwide
[27:12] Speaker 1: televised audience. You know that, among other things, she heard
[27:16] Speaker 1: Trump lunged at someone in a car on January sixth.
[27:20] Speaker 1: It was sort of this very dramatic, explosive moment. And
[27:24] Speaker 1: Pasentino subsequently was accused of sort of urging Cassidy Hutchinson
[27:31] Speaker 1: to mislead, if not be untruthful to the committee, a
[27:34] Speaker 1: claim that he has flat out denied. So he files
[27:37] Speaker 1: suit later saying that the committee and its staff leaked
[27:42] Speaker 1: information about his work with Cassidy to promote this false
[27:47] Speaker 1: narrative about him that he committed misconduct ethical breach. So
[27:51] Speaker 1: we have sort of two lawsuits that you know, on paper,
[27:54] Speaker 1: are very unconnected, but of a same feather.
[27:58] Speaker 2: The Biden administration fought both these cases, and one.
[28:03] Speaker 1: That's right, you know, part of why we this is
[28:05] Speaker 1: something we were looking at was they both started by
[28:09] Speaker 1: filing administrative claims with the agencies before going to court.
[28:14] Speaker 1: And it's a process that's sort of gotten rash attention
[28:17] Speaker 1: right now because it's the same process that Donald Trump
[28:19] Speaker 1: is pursuing at the administrative level trying to get according
[28:23] Speaker 1: to the New York Times, two hundred and thirty million dollars,
[28:27] Speaker 1: also because he says he was wronged by government actors. So,
[28:31] Speaker 1: you know, Flynn and Pasentinoes start with that process. They
[28:34] Speaker 1: say they don't hear back within the six month or
[28:37] Speaker 1: so period, so they sue, and the Justice Department under
[28:41] Speaker 1: President Biden fights both of these cases and says these are,
[28:45] Speaker 1: you know, not merit cases. They're legally deficient, they're procedurally deficient.
[28:51] Speaker 1: And in both instances the Justice Department wins. They get
[28:54] Speaker 1: an order dismissing Flynn's case, they get an order dismissing
[28:57] Speaker 1: Pasentino's case. In Lynn's case, the judge dismisses it but says,
[29:03] Speaker 1: I give you leave to file an invented complaint. You know,
[29:06] Speaker 1: you can come back and try again. So this happens
[29:08] Speaker 1: at the very end of twenty twenty four. Obviously there's
[29:11] Speaker 1: an election. Trump comes back to office, so Flynn's case
[29:15] Speaker 1: is not dead in the water, and his lawyers asked
[29:18] Speaker 1: for extensions, saying, you know, Trump is releasing new information
[29:21] Speaker 1: about them all er probe, we want to have more
[29:24] Speaker 1: time to update our complaint and the judge says it's fine.
[29:27] Speaker 1: DJ doesn't oppose this, and at the same time Pasentino
[29:31] Speaker 1: he appeals, he appeals his loss to the Eleventh Circuit.
[29:34] Speaker 1: You know, sort of interesting about this timeline is up
[29:37] Speaker 1: until this summer, DJ under Trump continues to fight his case.
[29:43] Speaker 1: So they file their brief in the Eleventh Circuit saying
[29:46] Speaker 1: the lower court judges order should be upheld. This was
[29:49] Speaker 1: not a meritorious case. The judge didn't make any errors.
[29:53] Speaker 1: So you know, both cases are sort of either in
[29:56] Speaker 1: limbo or continually, you know, being opposed by the Justice
[29:59] Speaker 1: departm And what we found then was by September there
[30:04] Speaker 1: are filings in both dockets saying one point eighty DJ
[30:09] Speaker 1: is now in settlement talks with both of them, and
[30:12] Speaker 1: this is the first time in either case that we've
[30:15] Speaker 1: seen that type of disclosure, and you know, there's very
[30:20] Speaker 1: little information on what's happening, what's being discussed. In both cases,
[30:26] Speaker 1: there are notices saying we need to pause because we
[30:28] Speaker 1: are now newly in settlement talks. And this is the
[30:32] Speaker 1: moment when I also sort of share that there is
[30:35] Speaker 1: a common feature of these cases, which is that Flynn
[30:37] Speaker 1: and Pasentino have the same lawyer. His name is Jesse Banal,
[30:41] Speaker 1: and he's represented Trump individually, He's represented his past campaign organizations.
[30:47] Speaker 1: He had been part of Sidney Powell's team representing Michael
[30:50] Speaker 1: Flynn back in the day. You know, it does work
[30:53] Speaker 1: for a number of conservative, Republican right leaning clients. So
[30:59] Speaker 1: you know, there is this common feature in both cases,
[31:02] Speaker 1: which is the same lawyer has a relationship with the
[31:05] Speaker 1: president and this administration, you know, by the end of
[31:08] Speaker 1: the summer is in settlement talks with the government.
[31:12] Speaker 2: Did anything happen to change things or that's not known.
[31:16] Speaker 1: You know, there's nothing in the public filings to indicate that,
[31:19] Speaker 1: and so far in our reporting that hasn't been confirmed.
[31:23] Speaker 1: You we just know that this is sort of an
[31:27] Speaker 1: ongoing effort dialogue issue that the president and his administration
[31:35] Speaker 1: have been very concerned about consistently since he took office,
[31:38] Speaker 1: which is working backwards and trying to undo decisions by
[31:45] Speaker 1: high level to mid level government actors across the federal
[31:49] Speaker 1: government that they see as wrong, illegal, evidence of political bias, weaponization.
[31:56] Speaker 1: It's a lot of different terms. It was a new
[31:59] Speaker 1: development in the cases, but a continuation of something that
[32:03] Speaker 1: has been a priority for this administration.
[32:06] Speaker 2: So the Justice Department is negotiating the deal. Is there
[32:10] Speaker 2: any oversight over the Justice Department's decision. Let's say the
[32:14] Speaker 2: Justice Department tomorrow says fifty million dollars to Michael Flynn,
[32:19] Speaker 2: any oversight at all?
[32:21] Speaker 1: You know, like most settlements in court, there is you know,
[32:24] Speaker 1: a final act of discretion by a judge when they
[32:28] Speaker 1: move to dismiss a case when there's a settlement. That's
[32:30] Speaker 1: not something that they can do unilaterally. But there is
[32:34] Speaker 1: very little room for judges to really probe that process
[32:38] Speaker 1: unless they feel like, you know, something happened on their
[32:43] Speaker 1: watch on the docket that requires intervention. But just the
[32:46] Speaker 1: fact of a settlement to resolve civil litigation, no matter
[32:50] Speaker 1: how far along things are. It's this is certainly not
[32:52] Speaker 1: the first administration to reverse the position, the litigating position
[32:57] Speaker 1: of the US government. When administration's change presidents of every party,
[33:01] Speaker 1: that happens, you know, it's not as if there's some
[33:04] Speaker 1: indication that that's something nefarious or illegal or wrong has happened.
[33:10] Speaker 1: You know, I think it was just a development that
[33:13] Speaker 1: you know, offered more evidence of sort of a broader
[33:18] Speaker 1: policy approach by the administration, which is, you know, are
[33:21] Speaker 1: there leavers of government that can be used to right
[33:24] Speaker 1: what the president sees as these major wrongs of his
[33:29] Speaker 1: sort of perceived political enemies. Whether we're talking about pardons, settlements,
[33:33] Speaker 1: declassifying information to make it public, Justice Department investigations, prosecutions,
[33:40] Speaker 1: there's sort of been this constant drumbeat of how does
[33:44] Speaker 1: the administration use the tools of government and in some cases,
[33:49] Speaker 1: taxpayer dollar to write what Trump sees as these wrongs.
[33:53] Speaker 2: This year, the Trump Justice Department reached a nearly five
[33:57] Speaker 2: million dollars settlement with the family of Ashley Babbitt, who
[34:02] Speaker 2: was shot during the January sixth riots at the Capitol.
[34:06] Speaker 2: Before Trump took office, Had the Biden administration been fighting
[34:10] Speaker 2: that lawsuit.
[34:11] Speaker 1: Yes, that's another one where under the previous administration, the
[34:16] Speaker 1: Justice Department had been seeking dismissal of I believe it
[34:19] Speaker 1: was some of the claims in that case. There was
[34:21] Speaker 1: a pending motion to dismiss and at a certain point
[34:25] Speaker 1: that position changed and the administration, once Trump took office,
[34:30] Speaker 1: entered into negotiations with the family and their attorneys to
[34:33] Speaker 1: reach a resolution. That process is not public information came
[34:37] Speaker 1: out about that only because there was sort of an
[34:39] Speaker 1: ancillary dispute related to lawyers who had been involved in
[34:43] Speaker 1: the case that landed on the docket ahead of that
[34:46] Speaker 1: settlement being announced, So there was sort of an early
[34:48] Speaker 1: preview of the fact that it was happening. That there's
[34:50] Speaker 1: no obligation by the government to share what it's talking
[34:54] Speaker 1: about why it's decided to enter into negotiations, and I
[34:58] Speaker 1: think it's also I should say the fact of settlement
[35:00] Speaker 1: talks is not a guarantee of a deal. You know,
[35:03] Speaker 1: there can be talks that don't yield an agreement in
[35:06] Speaker 1: the end. So we don't know how far along the
[35:10] Speaker 1: talks are with Flynn and Pasentino. We do know from
[35:12] Speaker 1: court filings that the government should put a hold on
[35:15] Speaker 1: whatever was happening. So there's been a delay up until
[35:18] Speaker 1: now from the past month. So there is just, you know,
[35:22] Speaker 1: a lot of secrecy built into this process by design.
[35:27] Speaker 2: There are claims with a political connection to Trump in
[35:32] Speaker 2: January sixth that the Justice Department is fighting that's right.
[35:37] Speaker 1: I mean, it's been a fascinating dynamic to watch on
[35:40] Speaker 1: play because throughout the campaign President Trump really took up
[35:45] Speaker 1: the cause of January sixth defendants as his own and
[35:49] Speaker 1: express support for them, you know, endorsed the thinking on
[35:53] Speaker 1: the right that these prosecutions were unwarranted, overblown, and he would,
[35:59] Speaker 1: you know, fload the idea of granting them clemency or pardons, commutations.
[36:06] Speaker 1: And there were high hopes from those who were involved
[36:11] Speaker 1: with these folks as their families, their attorneys, but also
[36:14] Speaker 1: activists in the conservative movement. And on day one, Trump
[36:18] Speaker 1: signed blanket clemency for those who had been convicted, charged
[36:23] Speaker 1: sentences commuted all but I think a handful of people
[36:26] Speaker 1: received clemency. But then there's been a bit of a
[36:30] Speaker 1: break and a lawyer for a number of these folks
[36:35] Speaker 1: named Mark McCloskey, he told us that they've been surprised
[36:40] Speaker 1: and frustrated that when they've gone and filed administrative claims
[36:44] Speaker 1: seeking damages for everything from you know, malicious prosecution, wrongful prosecution,
[36:50] Speaker 1: to the conditions of their prisonment for those who went
[36:54] Speaker 1: to jail, if that you know, FBI kicked down their
[36:57] Speaker 1: door in arresting them and broke in their house. You know,
[37:00] Speaker 1: there's a range of claims that you could make. He
[37:03] Speaker 1: says they've been rejected at least the first round or so,
[37:07] Speaker 1: and that they are preparing more and you know, encouraged
[37:12] Speaker 1: by some other actions by the administration to show support
[37:16] Speaker 1: for these folks. But there's been some consternation that it
[37:20] Speaker 1: hasn't been full throated. And of course we're going to
[37:24] Speaker 1: pay out money damages to the January sixth defendant. It
[37:28] Speaker 1: hasn't gone that far after the initial round of clemency,
[37:32] Speaker 1: and so there's maybe some uncertainty about whether this will
[37:35] Speaker 1: resolve in their favor. It's early to tell. I'm told
[37:39] Speaker 1: that hundreds more claims are getting ready to be filed soon.
[37:43] Speaker 1: But you know, that's been one area where the government
[37:46] Speaker 1: hasn't been sort of fully on their side. And there's
[37:49] Speaker 1: a lawsuit brought by some members of the Proud Boys
[37:52] Speaker 1: that the Justice Department is fighting under this administration. So
[37:57] Speaker 1: it hasn't been just a blanket.
[37:59] Speaker 2: Yes, once we find out more, it will be interesting
[38:02] Speaker 2: to see where they drew the line, if indeed they
[38:06] Speaker 2: do draw the line. Thanks Zoe. That's Bloomberg reporter Zoe Tilman.
[38:10] Speaker 2: Headlines are coming up right now, and that's it for
[38:14] Speaker 2: this edition of the Bloomberg Law Show. Remember you can
[38:16] Speaker 2: always get the latest legal news on our Bloomberg Law podcast.
[38:20] Speaker 2: You can find them on Apple Podcasts, Spotify, and at
[38:23] Speaker 2: www dot bloomberg dot com slash podcast, Slash Law, and
[38:28] Speaker 2: remember to tune into The Bloomberg Law Show every weeknight
[38:31] Speaker 2: at ten pm Wall Street Time. I'm June Grosso and
[38:35] Speaker 2: you're listening to Bloomberg

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